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Enantioselective synthesis of (+)-crocacin C. An example of a highly challenging mismatched double asymmetric ?-stannylcrotylboration reaction.

ABSTRACT: A concise, enantioselective synthesis of (+)-crocacin C is described, featuring a highly diastereoselective mismatched double asymmetric ?-stannylcrotylboration of the stereochemically demanding chiral aldehyde 9 with the bifunctional crotylborane reagent (S)-E-10. The total synthesis of (+)-crocacin C was accomplished in seven steps (longest linear sequence) starting from commercially available precursors.

SUBMITTER: Chen M

PROVIDER: S-EPMC3321065 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of (+)-crocacin C. An example of a highly challenging mismatched double asymmetric δ-stannylcrotylboration reaction.

Chen Ming M Roush William R WR

Organic letters 20120312 7

A concise, enantioselective synthesis of (+)-crocacin C is described, featuring a highly diastereoselective mismatched double asymmetric δ-stannylcrotylboration of the stereochemically demanding chiral aldehyde 9 with the bifunctional crotylborane reagent (S)-E-10. The total synthesis of (+)-crocacin C was accomplished in seven steps (longest linear sequence) starting from commercially available precursors. ...[more]

PMID: 22409510

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